3,4,5-Trimethoxybenzaldehyde → HCID 13338633, compound

HRID 2417925Notes

Reaction equation

HRID 2417925 reaction equation
[N:1]1[CH2:2][CH2:3][CH2:4][N:5]2[C:9]3[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][C:8]=3[S:7][C:6]=12.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH:20]=O.[BH4-].[Na+].[OH-].[NH4+]>O.C(O)(=O)C>[CH3:28][O:27][C:23]1[CH:22]=[C:19]([CH2:20][NH:14][C:11]2[CH:12]=[CH:13][C:8]3[S:7][C:6]4=[N:1][CH2:2][CH2:3][CH2:4][N:5]4[C:9]=3[CH:10]=2)[CH:18]=[C:17]([O:16][CH3:15])[C:24]=1[O:25][CH3:26]

Participants

7

Reactant 4

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 14923Ammonium HydroxideHCID 4311764Sodium borohydrideHCID 133385843,4-Dihydro-2H-pyrimido[2,1-b][1,3]benzothiazol-7-amine

Product 1

HCID 13338633HCID 13338633, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 6.2 parts of 3,4-dihydro-2H-pyrimido[2,1-b]benzothiazol-7-amine, 7.8 parts of 3,4,5-trimethoxybenzaldehyde and 60 parts of acetic acid are added portionwise 1.2 parts of sodium borohydride at a temperature between 18° and 20° C. Upon completion, stirring is continued for 30 minutes at room temperature. Water is added and the whole is alkalized with ammonium hydroxide. The product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is crystallized from ethanol, yielding 9.2 parts of 3,4-dihydro-N-(3,4,5-trimethoxyphenylmethyl)-2H-pyrimido[2,1-b]benzothiazol-7-amine; mp. 190.7° C.

Workup

  1. extractionThe product is extracted with trichloromethane
  2. customThe extract is dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-1300e9663e474a7da30444d9347e0e94
Source dataset
uspto-grants-1984_09
Patent number
US04471117

Reaction notes

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